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Actuating Cycloaromatization of a Bicyclo[7.3.1]enediyne by Annelation: An Example of Inverse Dependence on Bridge Atom Hybridization
Author(s) -
Nantz Michael H.,
Moss David K.,
Spence John D.,
Olmstead Marilyn M.
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980302)37:4<470::aid-anie470>3.0.co;2-q
Subject(s) - carbon atom , annulation , bicyclic molecule , chemistry , enediyne , inverse , cyclohexane , ring (chemistry) , atom (system on chip) , stereochemistry , mathematics , organic chemistry , catalysis , engineering , geometry , embedded system
Although the acetylenic carbon atoms in 2 are closer together than those in 1 , only the latter undergoes Bergman cyclization. In contrast, in analogous enediynes without an annelated cyclohexane ring a change in the hybridization of the bridging carbon atom from sp 2 to sp 3 leads to a dramatic increase in the cyclization rate.